Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 4-Bromopyridinium chloride | HCID 88100 | — |
| Reactant | HCID 91060211 | HCID 91060211 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 91588840 | HCID 91588840 | 76.6% |
Reaction Steps
A mixture of Example 14B (150 mg, 0.384 mmol), 4-bromopyridine hydrochloride (75 mg, 0.34 mmol), Pd2Cl2(PPh3)2 (27 mg, 0.0384 mmol), and CuI (18 mg, 0.093 mmol), was purged with nitrogen, treated with DMF (4 mL) and triethylamine (214 μL, 1.54 mmol), stirred at 50° C. for 20 hours, cooled to room temperature, treated with ethyl acetate (50 mL), washed with brine, dried (MgSO4), filtered, and concentrated. The residual oil was purified by flash column chromatography on silica gel with 2:1 ethyl acetate/hexanes to provide the desired product (122 mg, 68%). MS (APCI) m/e 469 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06831175B2 |
|---|
| Source dataset | uspto-grants-2004_12 |
|---|
| ORD ID | ord-78292f70298b4febad8201fb18182849 |
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| Source note | uspto-grants-2004_12 |
|---|
